Yu-Gi-Oh!

Was he a virgin? On one hand, he was a confident ambitious billionaire, on the other hand he was pathologically obsessed with a children's card game.

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Kaiba probably had sex once in his youth, decided it was too easy and a waste of time and instead invented a dragon-themed pocket pussy robot he can activate remotely at any time.

No. He was a pharaoh once.

He's rich and handsome. Being obsessed with a children's card game is quirky rather than creepy. Women would still fawn for Brad Pitt if he collected stamps

Seto found himself in front of Ishizu's door, hesitating before hearing a voice coming from inside: "Enter."
There was no backing out now. Pressing the access key, the metal door slid open, and Seto stepped through the threshold. Seated at her desk with her back to the tournament host, Ishizu's eyes peered over her anthology book to look into the mirror built into the wall. Dressed in a simple night gown, her neck was bare, having already given her Millennium Necklace away to the Pharaoh. Meeting Seto's eyes, she initiated the conversation. "Seto Kaiba, what an unexpected surprise," she declared. "To what do I owe this visit?"
"About our duel," Seto began, but he felt a familiar hesitation halt his speech once more. Ishizu gave a coy smile as she could see the curiosity in his eyes.
"Yes, it was a most impressive victory, Kaiba," she declared, closing her book and turning in her seat to face him. "I imagine you're not here simply to gloat?"
"Please, what do you take me for?" Seto questioned as he eyes narrowed on the Tombkeeper. He reached behind him, never breaking eye contact as he pressed the interior access button to close the door. "You may not know this, but all duels in this tournament are recorded and saved. I replayed ours, and I know you had 'Blast Held By a Tribute' set on the field. If it wasn't for my last minute hesitation, you would've won. I've had enough of your Egyptian fairy tales affecting my life. Coming this close to defeat is unacceptable."
With that, Kaiba pulled out his deck, and made his way towards Ishizu's desk, placing his deck down onto the surface adamantly.
"You want a rematch?" Ishizu inquired, looking from Kaiba's deck back to him. She reached into a golden jewelry box at the edge of her table, bringing from it her own dueling deck.
"No Millenium Items, no Egyptian magic, just you and I, skill versus skill," Seto dominantly laid out his terms. "Unless you're afraid you only got lucky the first time." 1/2

Ishizu gave a chuckle, closing her eyes and smiling. In his own way, Seto Kaiba was accepting his destiny, albeit in a manner she never would have suspected. Nevertheless, she welcomed this development.
"I noticed you failed to claim my rarest card after my defeat," Ishizu exclaimed as she looked up to meet Seto's gaze once more.
"My deck is already the most powerful on this blimp," Seto replied defiantly.
"So you believe. But very well, if you're not interested in my rarest card, then I have something else in mind. Should I still happen to lose this duel, Seto Kaiba, then I promise to surrender a prize worth more than my entire dueling deck," Ishizu declared as her eyes glazed over Kaiba's toned body.
"Looking forward to it," Seto Kaiba replied with a smirk.

He probably didn't care enough to lose it, but would have been very popular before his mental breakdown.

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He fucks his dragons every night

He eventually fucked Ishizu.

like jack he considers women to be an obstacle.

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